CN114380885A - 2 triterpenoids in caulis Sinomenii and preparation method thereof - Google Patents
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Abstract
The invention discloses 2 triterpenoids in caulis Sinomenii and a preparation method thereof, which comprises the steps of extracting chemical components in dried stems and leaves of caulis Sinomenii; extracting the triterpenoids by adopting cyclohexane and ethyl acetate in sequence to obtain a crude total sample of the triterpenoids; separating and purifying crude total samples of the triterpenoids, and respectively and repeatedly recrystallizing the eluted S2-1 and S2-4 to obtain the 3 beta-hydroxy-11, 13(18) -oleanolic diene, 3 beta-hydroxy-9 (11), 12-oleanolic diene which is a natural product obtained from the plant for the first time.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to 2 triterpenoids in caulis Sinomenii and a preparation method thereof.
Background
Caulis Sinomenii, named as traditional Chinese medicine. Is the stem and leaf of Sabianavira florae wall. The Chinese is mainly distributed in southwest of Guizhou, southeast to southwest of Yunnan, southwest of Guangxi and southwest; in southwest of Guizhou, Miao nationality and Buyi nationality use caulis Sinomenii of XIANHUAQINGFENGTENG to treat rheumatic arthralgia, traumatic injury pain, hepatitis, etc. Modern researches have shown that caulis Sinomenii contains flavonoids, alkaloids, triterpenes, saponins, etc. The triterpenoid is an important compound in nature and has wide physiological activity, and the research on the triterpenoid in the caulis sinomenii is rarely reported, so that the development and quality control of the caulis sinomenii medicinal material and the preparation thereof are limited.
Disclosure of Invention
Aiming at the defects, the invention aims to deeply research the caulis sinomenii and provide 2 triterpenoids in the caulis sinomenii and a preparation method thereof, and 2 triterpenoids are extracted by performing ultrasonic extraction, separation, purification and other processes on the overground part of the caulis sinomenii, so that the development and quality control of the caulis sinomenii medicinal material and the preparation thereof are facilitated.
In order to achieve the purpose, the invention adopts the following technical scheme:
2 triterpenoids in caulis Sinomenii, wherein the 2 triterpenoids are respectively 3 beta-hydroxy-11, 13(18) -oleanolic diene, 3 beta-hydroxy-9 (11), 12-oleanolic diene, the structural formula of the 3 beta-hydroxy-11, 13(18) -oleanolic diene is shown as a formula I, and the structural formula of the 3 beta-hydroxy-9 (11), 12-oleanolic diene is shown as a formula II:
further, the preparation method specifically comprises the following steps:
1) extraction:
taking dried stems and leaves of caulis Sinomenii, pulverizing, adding 5 times of 95% ethanol by weight, ultrasonically extracting for 3 times, each time for 4 hours, filtering, mixing extractive solutions, and concentrating the extractive solution to one tenth of the total extraction volume to obtain concentrated solution I;
adding purified water with equal volume amount into the concentrated solution, uniformly stirring to obtain a preparation solution, standing overnight at normal temperature, performing suction filtration on the preparation solution standing overnight, collecting filtrate, and concentrating the filtrate until no alcohol smell exists to obtain a concentrated solution II;
2) and (3) extraction:
adding purified water with the volume of 2 times of that of the concentrated solution II in the step 1) to dilute the concentrated solution II to obtain a diluent;
extracting the diluent with cyclohexane with the same volume to obtain extract I, extracting the extract I with ethyl acetate with the same volume to obtain extract II, and concentrating the extract II to obtain an extract;
dissolving the extract in 2 times of acetone, filtering to remove insoluble substances to obtain solution, and standing at 7 deg.C overnight;
filtering the solution which is left overnight, collecting filtrate, and concentrating the filtrate to dryness to obtain a crude total sample of the triterpenoid;
3) separation and purification:
adding the mixed solvent I with the weight of 1.5 times of the crude total sample of the triterpenoid in the step 2) for dissolving, then adding column chromatography silica gel with the weight equal to that of the crude total sample, uniformly stirring, volatilizing the mixed solvent I to obtain a purified sample I, taking the column chromatography silica gel with the weight of 30 times of the purified sample, carrying out wet column packing, carrying out isocratic elution by taking the mixed solvent II as an initial solvent, collecting 1 section for each 8 column chromatography retention volumes, collecting 2 sections of samples in total, and respectively naming the samples as S1 and S2;
dissolving S2 with dichloromethane with the volume of 1.5 times of that of S2, adding column chromatography silica gel with the weight equal to that of S2, stirring uniformly, volatilizing dichloromethane solvent to obtain a purified sample II, taking the column chromatography silica gel with the weight 20 times of that of the purified sample II, filling the column by a wet method, carrying out isocratic elution by taking a mixed solvent III as an initial solvent, collecting 1 section for every 4 column chromatography retention volumes, and collecting 4 sections of samples which are named as S2-1, S2-2, S2-3 and S2-4 respectively;
repeated recrystallization of S2-1 gave compound 1, and repeated recrystallization of S2-4 gave compound 2.
Further, the compound 1 is 3 beta-hydroxy-11, 13(18) -oleanolic diene, the structural formula of which is shown in a formula I, and the compound 2 is 3 beta-hydroxy-9 (11), 12-oleanolic diene, the structural formula of which is shown in a formula II.
Further, the mixed solvent I is dichloromethane: the mixed solvent II is a mixed solution of dichloromethane and acetone in a ratio of 15:1, and the mixed solvent III is a mixed solution of dichloromethane and acetone in a ratio of 10: 1.
Further, the specification of the column chromatography silica gel is 100-300 meshes.
Further, the temperature of the ultrasonic extraction was 60 ℃.
By adopting the scheme, the invention has the following advantages:
1. according to the invention, the overground part of the caulis Sinomenii is taken as a raw material, 2 triterpenoids are firstly obtained from the caulis Sinomenii, through the steps of extraction, separation and purification and the like, and the 2 triterpenoids are respectively identified to be 3 beta-hydroxy-11, 13(18) -oleanoline and 3 beta-hydroxy-9 (11), 12-oleanoline, so that the development and quality control of the caulis Sinomenii medicinal material and a preparation thereof are facilitated, and chemical basis and substance reference are provided for the comprehensive development of the caulis Sinomenii medicinal material and the research of natural plant pharmacological activity.
2. The 2 triterpenoids obtained from the caulis Sinomenii have small polarity difference, are easy to generate mixed crystals and are difficult to separate, and the method finds out practical separation conditions, so that the extraction and separation method for separating the two triterpenoids has the advantages of simple operation, low cost, mild used reagents, small harm to human bodies, high purity of the obtained compounds and less impurities.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention. The objectives and other advantages of the invention will be realized and attained by the structure particularly pointed out in the written description and claims hereof.
Drawings
FIG. 1 is a thin layer chromatogram of S1 of the present invention;
FIG. 2 is a thin layer chromatogram of S2 of the present invention;
FIG. 3 is a thin layer chromatogram of a sample before combination S2-1 and a sample before combination S2-4 according to the present invention;
FIG. 4 is a carbon spectrum of 3 β -hydroxy-11, 13(18) -oleanolic diene of the present invention;
FIG. 5 is a carbon spectrum of 3 β -hydroxy-9 (11), 12-oleanolic diene according to the present invention;
FIG. 6 is a crystal diagram of 3 β -hydroxy-11, 13(18) -oleanolic diene, 3 β -hydroxy-9 (11), 12-oleanolic diene according to the present invention.
Detailed Description
The present invention will now be described in detail with reference to the drawings and examples, which are not intended to limit the invention in any way, except as specifically stated, reagents, methods and apparatus are conventional in the art.
Example 1: preparation of 2 triterpenoids in caulis Sinomenii
1. Experimental methods
1) Extraction:
taking dried stems and leaves of caulis Sinomenii, pulverizing, adding 5 times of 95% ethanol, ultrasonically extracting at 60 deg.C for 3 times (4 hr each time), filtering, mixing extractive solutions, and concentrating the extractive solution to one tenth of the total extraction volume to obtain concentrated solution I;
adding purified water with equal volume to the concentrated solution, uniformly stirring to obtain a preparation solution, standing overnight at normal temperature, performing suction filtration on the preparation solution standing overnight by using a Buchner funnel, collecting filtrate, and concentrating the filtrate until no alcohol smell exists to obtain a concentrated solution II;
2) and (3) extraction:
adding purified water with the volume of 2 times of that of the concentrated solution II in the step 1) to dilute the concentrated solution II to obtain a diluent;
extracting the diluent with cyclohexane with the same volume to obtain extract I, extracting the extract I with ethyl acetate with the same volume to obtain extract II, and concentrating the extract II to obtain an extract;
dissolving the extract in 2 times of acetone, filtering to remove insoluble substances to obtain solution, and standing at 7 deg.C overnight;
carrying out suction filtration on the overnight-placed dissolved solution by using a Buchner funnel, collecting filtrate, and concentrating the filtrate to dryness to obtain a crude total sample of the triterpenoid;
3) separation and purification:
adding a 1.5-fold amount of dichloromethane to the crude total sample of triterpenoids in step 2): dissolving the mixed solvent I of acetone 1:1, adding column chromatography silica gel (100-300 meshes) with the weight equal to the weight of the crude total sample, uniformly stirring, and volatilizing dichloromethane: obtaining a purified sample I by taking a mixed solvent I with acetone being 1:1, taking column chromatography silica gel (100-300 meshes) which is 30 times the weight of the purified sample, filling the column by a wet method, carrying out isocratic elution by taking a mixed solvent II with dichloromethane being 15:1 as an initial solvent, collecting 1 section of sample in each 8 column chromatography retention volumes, and collecting 2 sections of samples in total, wherein the samples are named as S1 and S2 respectively;
dissolving S2 with dichloromethane with the volume of 1.5 times of that of S2, adding column chromatography silica gel (100-mesh and 300-mesh) with the weight equal to that of S2, uniformly stirring, volatilizing dichloromethane solvent to obtain a purified sample II, taking column chromatography silica gel with the weight 20 times of that of the purified sample II, loading the column by a wet method, carrying out isocratic elution by using a mixed solvent III of dichloromethane and acetone which are 10:1 as an initial solvent, collecting 1 section for every 4 reserved volumes of column chromatography, collecting 4 sections of samples in total, and respectively naming the samples as S2-1, S2-2, S2-3 and S2-4;
repeated recrystallization of S2-1 gave compound 1 with the crystallization effect shown as T1-6 in FIG. 6, and repeated recrystallization of S2-4 gave compound 2 with the crystallization effect shown as E12 in FIG. 6.
2. Results of the experiment
The yield of compound 1 was about 1.3%; the yield of compound 2 was about 0.8%.
Example 2: screening experiments
1. Experimental methods
1.1 thin layer chromatography of S1, S2, respectively, using dichloromethane: the mixture was developed under the condition of 3:1 cyclohexane, and developed by spraying vanillin concentrated sulfuric acid.
1.2 thin layer chromatography was performed on the combined S2-1, S2-2, S2-3 and S2-4 samples using cyclohexane: dichloromethane: development was performed under the condition of methanol at 6:2:0.6, and color development was performed by spraying vanillin concentrated sulfuric acid.
2. Results of the experiment
2.1 As shown in FIGS. 1 and 2, S1 has more mixed impurities and less purple-red spots, S2 has purple-red spots in the Rf value range of 0.2-0.4, and the sample has stronger crystallinity but lower purity, and needs to be further separated by silica gel column chromatography, so S2 is selected for next purification.
2.2 As shown in FIG. 3, a series of magenta spots appeared at an Rf value of 0.45, and a series of magenta spots also appeared at an Rf value of 0.41. The same spots were combined to form the S2-1 sample and the S2-4 sample. Meanwhile, the samples of the S2-2 and S2-3 parts are mixtures of two substances, so that the samples are not suitable for recrystallization.
Example 3: structural identification
1. Experimental methods
And (3) respectively carrying out structural identification on the compound 1 and the compound 2 by utilizing nuclear magnetic resonance carbon spectrum.
2. Results of the experiment
As shown in fig. 4, compound 1: white crystals (trichloromethane).13C-NMR(150MHz,CDCl3) 38.03(C-1),27.23(C-2),79.06(C-3),40.25(C-4),54.24(C-5),18.45(C-6),32.48(C-7),38.9(C-8),54.88(C-9),36.71(C-10),125.29(C-11),125.77(C-12),138.1(C-13),42.36(C-14),24.45(C-15),35.31(C-16),34.68(C-17),133.38(C-18),36.71(C-19),33.09(C-20),36.17(C-21),38.03(C-22),27.9(C-23),15.09(C-24),16.6(C-25),17.96(C-26),20.25(C-27),25.42(C-28), 32.48-29 (C-29),24.14 (C-30). The above data are consistent with literature reports, so compound 1 was identified as 3 β -hydroxy-11, 13(18) -oleanoline;
as shown in fig. 5, compound 2: white crystals (trichloromethane).13C NMR(150MHz,CDCl3) δ: 37.15(C-1), 28.27(C-2), 78.73(C-3), 38.94(C-4), 51.16(C-5), 18.37(C-6), 31.14(C-7), 38.77(C-8), 154.33(C-9), 40.86(C-10), 115.75(C-11), 120.71(C-12), 147.13(C-13), 42.78(C-14), 25.66(C-15), 27.24(C-16), 32.16(C-17), 45.59(C-18), 46.91(C-19), 29.74(C-20), 34.62(C-21), 37.07(C-22), 28.74(C-23), 15.70(C-24), 20.09(C-25), 20.98(C-26), 25.31(C-27), 28.74(C-28), 23.73(C-29), 33.22 (C-30). The above data are consistent with literature reports, so compound 2 was identified as 3 β -hydroxy-9 (11), 12-oleanolic diene.
Finally, the description is as follows: although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art will understand that various changes, modifications and substitutions can be made without departing from the spirit and scope of the invention as defined by the appended claims. Any modification, equivalent replacement, or improvement made without departing from the spirit and principle of the present invention shall fall within the protection scope of the present invention.
Claims (6)
1.2 triterpenoids in caulis Sinomenii, which are characterized in that the 2 triterpenoids are respectively 3 beta-hydroxy-11, 13(18) -oleanolic diene, 3 beta-hydroxy-9 (11), 12-oleanolic diene, the structural formula of the 3 beta-hydroxy-11, 13(18) -oleanolic diene is shown as a formula I, and the structural formula of the 3 beta-hydroxy-9 (11), 12-oleanolic diene is shown as a formula II:
2. the preparation method of 2 triterpenoids in caulis Sinomenii, according to claim 1, is characterized in that the preparation method specifically comprises the following steps:
1) extraction:
taking dried stems and leaves of caulis Sinomenii, pulverizing, adding 5 times of 95% ethanol by weight, ultrasonically extracting for 3 times, each time for 4 hours, filtering, mixing extractive solutions, and concentrating the extractive solution to one tenth of the total extraction volume to obtain concentrated solution I;
adding purified water with equal volume amount into the concentrated solution, uniformly stirring to obtain a preparation solution, standing overnight at normal temperature, performing suction filtration on the preparation solution standing overnight, collecting filtrate, and concentrating the filtrate until no alcohol smell exists to obtain a concentrated solution II;
2) and (3) extraction:
adding purified water with the volume of 2 times of that of the concentrated solution II in the step 1) to dilute the concentrated solution II to obtain a diluent;
extracting the diluent with cyclohexane with the same volume to obtain extract I, extracting the extract I with ethyl acetate with the same volume to obtain extract II, and concentrating the extract II to obtain an extract;
dissolving the extract in 2 times of acetone, filtering to remove insoluble substances to obtain solution, and standing at 7 deg.C overnight;
filtering the solution which is left overnight, collecting filtrate, and concentrating the filtrate to dryness to obtain a crude total sample of the triterpenoid;
3) separation and purification:
adding the mixed solvent I with the weight of 1.5 times of the crude total sample of the triterpenoid in the step 2) for dissolving, then adding column chromatography silica gel with the weight equal to that of the crude total sample, uniformly stirring, volatilizing the mixed solvent I to obtain a purified sample I, taking the column chromatography silica gel with the weight of 30 times of the purified sample, carrying out wet column packing, carrying out isocratic elution by taking the mixed solvent II as an initial solvent, collecting 1 section for each 8 column chromatography retention volumes, collecting 2 sections of samples in total, and respectively naming the samples as S1 and S2;
dissolving S2 with dichloromethane with the volume of 1.5 times of that of S2, adding column chromatography silica gel with the weight equal to that of S2, stirring uniformly, volatilizing dichloromethane solvent to obtain a purified sample II, taking the column chromatography silica gel with the weight 20 times of that of the purified sample II, filling the column by a wet method, carrying out isocratic elution by taking a mixed solvent III as an initial solvent, collecting 1 section for every 4 column chromatography retention volumes, and collecting 4 sections of samples which are named as S2-1, S2-2, S2-3 and S2-4 respectively;
repeated recrystallization of S2-1 gave compound 1, and repeated recrystallization of S2-4 gave compound 2.
3. The method for preparing 2 triterpenoids in caulis Sinomenii, as claimed in claim 2, wherein the compound 1 is 3 β -hydroxy-11, 13(18) -oleanoline with a structural formula shown in formula I, and the compound 2 is 3 β -hydroxy-9 (11), 12-oleanoline with a structural formula shown in formula II.
4. The method for preparing 2 triterpenoids in caulis Sinomenii as claimed in claim 3, wherein the mixed solvent I is dichloromethane: the mixed solvent II is a mixed solution of dichloromethane and acetone in a ratio of 15:1, and the mixed solvent III is a mixed solution of dichloromethane and acetone in a ratio of 10: 1.
5. The method for preparing 2 triterpenoids in caulis Sinomenii as claimed in claim 4, wherein the specification of the column chromatography silica gel is 100-300 mesh.
6. The method for preparing 2 triterpenoids in caulis Sinomenii, according to claim 5, wherein the temperature of ultrasonic extraction is 60 ℃.
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